STEREOSELECTIVE ADDITION OF LITHIOETHYLACETATE TO BOC-L-PROLINAL. A CONVENIENT CHIRAL SYNTHETIC BUILDING BLOCK FOR THE PYRROLIZIDINE ALKALOID RING SYSTEM

DOI: 10.1016/S0040-4039(00)84853-4

Source and publish data:

Tetrahedron Letters p. 3577 - 3580 (1986)

Update date:2022-08-10

Topics:

Authors:

Hanson, Gunnar J.

Baran, John S.

Lindberg, Thomas

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Article abstract of DOI:10.1016/S0040-4039(00)84853-4

Aldol condensation of lithioethyl acetate with Boc-L-prolinal proceeds stereoselectively to give R,S diastereomer 2.Acidolysis of the Boc group and lactamization gives crystalline 3 which possesses the pyrrolizidine alkaloid skeleton.Saponification and acidolysis of 2 yields 7, a novel GABA analogue.

Full text of DOI:10.1016/S0040-4039(00)84853-4

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